Ryan Sheckler: one of the most successful professional skateboarders in the history of the sport | Photo: Red Bull

Ryan Sheckler is one of the most influential skateboarding figures of the 21st century, attracting high-profile brands and sports companies.

He's a do-or-die skater, a life-or-death-spot athlete - a rider followed by millions of fans.

Skate videographer Ira Ingram describes him as "a psychopath" - someone who is obsessively pushing the boundaries of what's possible.

But who exactly is this tattoed madman?

Ryan Sheckler was born on December 30, 1989, in San Clemente, California.

His father, Randy Sheckler, and mother, Gretchen Sheckler, had three boys - Ryan and his younger brothers Shane and Kane.

Ryan Sheckler started skateboarding when he was just 18 months old.

He grew up in a surf-and-skate community, and as a toddler, he was a little rascal. At the age of three, he got electrocuted really badly.

Meanwhile, Ryan had been diagnosed with attention deficit disorder (ADD), a condition that channeled him toward outdoor physical activities.

To his surprise, Tony Hawk showed up at his sixth birthday party.

"My dad somehow managed to get in touch with him via email, invited him, and Tony said he would come as long as he got chocolate cake," revealed Sheckler.

Ryan landed his first kickflip at age six, and by the time he was eight, he was already looking for endorsement and sponsorship deals.

Etnies and Oakley were his first sponsors. Ryan was excited and believed he could turn pro at 21.

But he was wrong. At 13, the teenage prodigy had turned pro. "It was quicker than I thought," Sheckler stressed.

"But I just wanted to be in the same skatepark with the dudes I looked up to."

Ryan Sheckler: he won his first gold medal at the X Games aged 13 | Photo: X Games

The X Games and Professionalism

Ryan Sheckler is one of the first stars of the X Games, the highly successful extreme sports series produced and broadcast by ESPN.

Aged 13, he won his first gold medal at the soon-to-be iconic competition.

"It was the defining moment for the start of my career as a professional skateboarder," says Sheckler.

In that same year, 2003, he won all contests he participated in and was riding for Rodney Mullen and Daewon Song's Almost Skateboards.

A fierce competitive skater, Sheckler always aimed for the top spot on the podium in any contest he entered.

From his early years, Ryan always made complex skateboard tricks look easy to land.

Whether he was flying over huge gaps and stairs or grinding handrails for dozens of meters, Sheckler became an all-around skateboarder, comfortable in any environment, be it a skatepark, ditch, bowl, city street, or offroad terrain.

"Skateboarding is pure freedom. I get on my board, and I don't have to skate like anyone else," Sheckler once said.

"I don't have to try the tricks anyone else is trying. I can clear my head and just skate my game."

So, before he reached the minimum age required to obtain a driver's license, Sheckler already had multiple lucrative contracts coming in.

"At a young age, money was a freedom ticket. If I wanted to take my family out to dinner, I could," Ryan stated.

"But money didn't really have a grip on me until I was 18. It wasn't important to me until I was getting ready to buy a house or jewelry."

"I've wasted over a million dollars for bottle service, tables at clubs, penthouse suits, flying private, and these material things."

"I look back on now, and I wish I would have saved that to buy some real estate or assets that are actually creating revenue and not burning it or putting in in the foundation."

Sponsors wanted him to travel and be a part of the professional skateboarding circuit for two-thirds of the year.

In 2007, Sheckler left Almost and joined Plan B.

"I didn't have friends that were of my age. Of all my friends were 20 and above. But I wanted to skate. I stayed focused. I had very strong family morals," recalls Sheckler.

"I never drank, and I never smoked when I was on the road. But I missed my family, my friends, and I wanted to be home."

Ryan got back to school, but halfway through the year, he already wanted to return to his professional duties.

Meanwhile, he learned wrestling.

"Wrestling taught me how to fall better on my skateboard. A lot of people don't realize that you really need to learn how to fall from huge obstacles."

Ryan Sheckler: a do-or-die skater | Photo: Red Bull

The Reality Show and A Lesson Learned

As a young kid, Sheckler was already signing autographs and earning thousands of dollars every month.

His mother helped him manage fame, fortune, and envy from opponents and haters.

In August 2007, he debuted his three-season MTV show, "Life of Ryan," which only added fuel to the fire.

"I was getting a weird vibe from other professional skateboarders. The dudes I looked up to were kind of not too psyched on what I was doing," Ryan admitted.

Was he selling out the industry?

"I'm one person. One person can't destroy an activity that's purely supposed to be freedom anyways."

But the "Life of Ryan" took a path that Ryan hadn't signed up for. There was too much acting and forced breakups with his girlfriend.

"It traumatized me. I didn't get into a relationship after the show until I was 25 because I didn't want to go through a breakup again."

"I have a heart and strong emotions. I do not like hurting people's feelings. And doing it for the sake of television rocked me."

At a certain point, he even got a new nickname - "Crying Ryan." Why? For crying about hearing that his parents were going to get divorced.

Sheckler says he learned the lessons but doesn't regret doing it. He was just 17.

The Costco Gap: Ryan Sheckler landed a 16-foot high jump into concrete located in Orange County | Photo: Etnies/Atiba

Achievements and Inspiration

Ryan has never spent much at home. He's been a professional athlete with a busy agenda ever since.

In April 2008, the young skater successfully jumped over the 55-foot (17-meter) gap on Bob Burnquist's Mega Ramp.

In June, Ryan Sheckler landed the cover of The Skateboard Mag after clearing the "Costco Gap," a 16-foot jump into concrete located in Orange County.

At the time, nobody could do it.

"When I showed up, I instantly knew I could do it. And it ended up being one of the biggest kickflips in skateboarding," the athlete later explained.

"The feeling of rolling away is indescribable. It's euphoria."

Sheckler has always been honest about his dreams. He wanted to touch the stars and become a reference and a legend.

By the end of "Life of Ryan," Sheckler was contacted by the Make A Wish Foundation. There was a young girl named Casey with throat cancer who would love to meet him.

And so he traveled to Texas to get to know her.

"It was the first time I realized that my influence has been positive for someone. And from that moment on, I thought I had to give back," declares Sheckler.

Ryan started a fundraiser for the Children's Cancer Research Fund (CCRF) and ended up gathering $240,000.

The San Clemente skater had a new purpose for his life.

In 2008, he founded the Sheckler Foundation with a clear mission - to support causes that benefit the lives of children and injured action sports athletes.

"They are the biggest inspiration to me because they've got no legs, and they're skating with prosthetic legs for six hours straight - with no complaints."

"They're dropping in on 10-foot quarter-pipes, they're falling, they're positive, and nothing can hold them back."

But Ryan's wheels kept moving, and with an X Games street skateboarding gold medal in his pocket, he was ready to take over the world.

In 2009, the green-eyed skater failed to land off a 12-stair drop and shattered his ankle at the famous competition.

One year later, Sheckler does it again. He wins another X Games gold medal, a feat that was witnessed by more than a million TV viewers.

In 2011, he launched "Scheckler Sessions," a skate series produced by one of his major sponsors, Red Bull.

Before going through his darkest period, Ryan won the Dew Tour three times (2012, 2013, and 2014).

Ryan Sheckler: one of the finest and most influential skateboarders of the 21st century | Photo: Ethika

The Road to Sobriety

Then, already in his 20s and with a stagnant career, Sheckler began drinking - day after day.

Suddenly, he realized he had in front of him one of the biggest challenges he had ever faced - to get sober.

"I couldn't stop drinking. I wanted to, but I couldn't. I remember being in Oslo [Norway] and not wanting anything to do with skateboarding," underlines the multiple-time X Games medalist.

"I didn't want to be in the public's eye anymore at all."

His mother played a critical role in putting an end to his son's addiction; Olympic gold medalist Michael Phelps also reached out to lend him support.

Ryan spent four years sober.

However, when he thought he had kicked alcoholism out of his life, a drink was enough for a relapse to occur.

"It was my 30th birthday, and I had taken so much time off of drinking that I was like: 'Maybe I got this; maybe I can drink normally.'"

His mother, once again, saved him. She was - and has always been - the pillar.

"She's my best friend. She's always shown me love and grace and has always been the one I can trust. If something's going on, I call her first."

Ryan Sheckler: an all-around street, bowl, and park skateboarder | Photo: Red Bull

Skateboarding as a Way of Living

Ryan always worked on competition runs for months before each contest.

In his teenage years, and as part of his workout routine, he rode bikes, ran, and did a lot of weight training.

"People don't know how much willpower that takes to fall really hard and to get back up and try it again. It teaches your brain how to never give up," notes Sheckler.

"I visualize all my tricks. I just sit with my eyes closed and visualize over and over the body position, the landing, how I want it to do it, how I want to look to the people."

Today, Sheckler is a multimillionaire and a global skateboarding star with millions of followers all over the world.

Believe it or not, skateboarding is still his childhood pastime.

The only difference is that he was able to transform his name into a recognizable, respected, and valuable brand.

"I love going out to a contest and getting the fans what they want to see."

One of the things that have kept Ryan Sheckler on top of his game is that he has always found inspiration and learned from youth.

And he trains and practices a lot, even though he's never at work - Sheckler is enjoying every moment as if he was starting all over again.

And for skating a lot, let's just say the California phenom has already broken his elbows ten times, suffered medial collateral ligament (MCL) injuries on both knees, anterior cruciate ligament (ACL) injuries, a partial meniscus tear, a Lisfranc injury on his right foot, broke his left foot and ankle, and right ankle twice, and suffered several concussions.

Fortunately, his longtime strength and conditioning coach, John Welch, has helped him recover from the major injuries and also after his drinking habit years.

"I've always been impressed with Ryan's work ethic. He's always giving himself incredible structure and sticks to the plan," Welch underlined.

Ryan has his own indoor skatepark, where he spends a lot of time perfecting his skills, fine-tuning maneuvers, and adding variations to his winning runs.

It's his private laboratory - a place for experimentation and innovation.

And he has many tattoos. "Most were planned out, some were spontaneous," he once revealed.

The first one was the word "Sheckler" on his back.

And then, it was, "If I get hurt, I get a tattoo. And I've been hurt a lot, so I'm almost filled up."

If he wasn't riding a skateboard, Mr. Sheckler was probably racing cars. Why? "I just like going fast."

Ryan Sheckler: a suicidal tail drop in Taipei, Taiwan on April 17, 2019 | Photo: Red Bull

A Businessman and a Christian

Ryan Sheckler diversified his business ventures with multiple commercial interests in and out of skateboarding.

Sandlot Times, Palm Springs Surf Club, and Ethika are only the tip of the iceberg of his investments.

His net worth is estimated at $100 million.

Ryan Sheckler often credits his longtime agent, Steve Astephen, for helping him build an empire and making him a millionaire.

Shecler's most famous nickname is "Shecks."

He is the star of four video games: Tony Hawk's Underground 2, Tony Hawk's American Wasteland, Tony Hawk's Project 8, and Tony Hawk's Proving Ground.

Ryan has publicly supported the inclusion of skateboarding in the Olympic Games.

"If a kid that has never skateboarded is watching the Olympics and sees skateboarding and decides to become a skateboarder - if only one kid does that - then it's a success."

Sheckler also discovered golf, a sport that "it's almost like a meditation."

Ryan is a Christian and sees marriage through the eyes of the Bible.

He is in a relationship with Abigail Baloun. The couple advocates no premarital sex.

"We take the sin out of the relationship and leave it wholesome," emphasizes Sheckler.

"It allows us to grow into believers in Christ but also allows us to look forward to something possibly super magical in the future. It's supposed to be special."

But why does religion play an important role in his life?

"I've had a very fulfilled life. When I look at it, a lot of that fulfillment that I thought was pure fun, it was sin. I look at it now, and I want to live a life that is pleasing to the Lord," the skater concludes.

"I am now a born-again Christian. I've always been a believer, but I wasn't following the practices. I wasn't absorbing the lessons of the Bible. And I wanted to change. Something was calling, and it was Jesus."

Ryan Sheckler is on Facebook (@RyanSheckler), Instagram (@shecks), Twitter (@RyanSheckler), and YouTube (@ryanshecklervideo).

Top Stories

Why hasn't anyone thought about this yet?

If there's one iconic heelflip that changed a skater's life forever, it's Rayssa's. Here's how a young girl's dream became more real than reality itself.

"Back to the Future" is a timeless masterpiece. Interestingly, the franchise features several famous skateboard-related appearances.

If there's a challenge that puts a skateboarder's fear to the test, it is a stair gap. In 2015, Aaron Homoki defied the odds and cleared an infamous staircase in France.